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Intensely potent morpholinyl anthracyclines.

E M Acton, G L Tong, C W Mosher

    Journal of Medicinal Chemistry
    |May 1, 1984
    PubMed
    Summary
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    A novel doxorubicin analogue, 3'-deamino-3'-(3-cyano-4-morpholinyl)doxorubicin, shows significantly higher potency against tumors and reduced cardiotoxicity in preclinical models. This compound offers potential for improved cancer chemotherapy.

    Area of Science:

    • Medicinal Chemistry
    • Oncology
    • Pharmacology

    Background:

    • Doxorubicin is a widely used anthracycline chemotherapy agent.
    • Doxorubicin exhibits significant cardiotoxicity, limiting its clinical application.
    • Development of novel analogues with improved efficacy and safety profiles is crucial.

    Purpose of the Study:

    • To synthesize and evaluate a new doxorubicin analogue, 3 '-deamino-3 '-(3-cyano-4-morpholinyl)doxorubicin.
    • To assess the antitumor potency and toxicity profile of the novel analogue compared to doxorubicin.

    Main Methods:

    • Reductive alkylation of doxorubicin and daunorubicin with 2,2 ' - oxybis [acetaldehyde].
    • Separation of morpholinyl nitrile byproducts from morpholino derivatives.
    • Evaluation of antitumor activity in cell culture and mouse models.

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  • Assessment of cardiotoxicity in mice.

    • Main Results:

    • The new analogue demonstrated 100 to 1000 times greater potency than doxorubicin against tumors.
    • The analogue was effective via intraperitoneal, intravenous, and oral administration.
    • No chronic myocardial lesions were observed in mice treated with the analogue.

    Conclusions:

    • 3 '-Deamino-3 '-(3-cyano-4-morpholinyl)doxorubicin represents a promising new anthracycline derivative.
    • This analogue offers superior antitumor activity and a favorable safety profile, particularly regarding cardiotoxicity.
    • Further investigation into this new class of anthracyclines is warranted.